|Jmol-3D images||Image 1|
|Molar mass||90.12 g mol−1|
|Melting point||−58 °C (−72 °F; 215 K)|
|Boiling point||85 °C (185 °F; 358 K)|
|Solubility in water||miscible|
|EU classification||Flammable (F)
Repr. Cat. 2
|R-phrases||R60, R61, R11, R19, R20|
|Flash point||−2 °C (28 °F; 271 K)|
|Related compounds||Ethylene glycol
Diethylene glycol dimethyl ether
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water.
The lowest energy form of dimethoxyethane in the gas phase is the gauche, rather than the anti conformer.
Monoglyme may be manufactured by a number of methods:
- via the Williamson ether synthesis — reacting the sodium salt of 2-methoxyethanol (previously prepared by reaction with sodium) with chloromethane:
- 2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2↑
- CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
- via the alkylation of 2-methoxyethanol with dimethyl sulfate
- by the cleavage of ethylene oxide in presence of dimethyl ether. This reaction is catalyzed by Lewis acids (e.g. boron trifluoride or its complex with dimethyl ether). This route is not particularly selective and produces diglyme, triglyme, tetraglyme, and other glymes as a by-products. The reaction mixture is separated by distillation:
- CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3
Applications as solvent and ligand
Together with a high-permittivity solvents (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent.
Dimethoxyethane is often used as a higher boiling alternative to diethyl ether and THF. Dimethoxyethane forms chelate complexes with cations and acts as a bidentate ligand. It is therefore often used in organometallic chemistry like Grignard reactions, hydride reductions, and palladium-catalyzed reactions like Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.
- D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
- K. Dreisch, C. Andersson, C. Stalhandske "Synthesis and structure of dimethoxyethane-dichlorodioxo-tungsten(VI)—a highly soluble derivative of tungsten dioxodichloride" Polyhedron 1991, volume 10, p. 2417. doi:10.1016/S0277-5387(00)86203-8